Oakland Vacations from $420
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Your Oakland Vacation
From its cycling to its walking, there's tons to love about Oakland. Book a customized Oakland vacation package and get ready to fall for the delights of this neighborhood. When it's time to head out and explore, you'll find lots of big-name attractions nearby including Acrisure Stadium, University of Pittsburgh and PNC Park. Tick off one, two or all during your trip to Oakland. No matter your travel plans or budget, booking the ultimate Oakland vacation is simple with Expedia.
The Latest Oakland Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Hampton Inn & Suites Pittsburgh-Downtown
Downtown Pittsburgh
Price was $876, price is now $718 per person
$718
per person
Dec 4 - Dec 7
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Pittsburgh (PIT)
9.4/10 Exceptional! (1,366 reviews)
The property was clean and updated in a great location. The price was great compared to other properties in the area and included free parking and breakfast. The front desk staff was so friendly! We had one small issue with housekeeping and the manager more than made up for it. I’d definitely stay here again
Reviewed on Nov 3, 2026
Joinery Hotel Pittsburgh, Curio Collection by Hilton
Downtown Pittsburgh
Price was $607, price is now $500 per person
$500
per person
Jan 4 - Jan 8
found 1 hour ago
Roundtrip flight included
Dallas (DFW) to Pittsburgh (PIT)
8.6/10 Excellent! (1,697 reviews)
No choices for eating or picking up snack items etc. Walkable distance to Acrisure Stadium but seemed to be quite unsafe as I was approached by several people asking for handouts.
Reviewed on Nov 3, 2026
Where to stay in Oakland
Find the best Oakland areas and neighborhoods for the activities you enjoy most. Learn more about Oakland
Downtown Pittsburgh
2 out of top 10 points of interest in this area
Discover the urban downtown center, home to historic sites like Point State Park and the Cultural District. Enjoy diverse shopping options and easy access to public transportation, including the "T" light rail and bus networks.
Oakland Hotel Deals
Courtyard by Marriott Pittsburgh University Center
100 Lytton Avenue Pittsburgh PA
$122 nightly
The price is $139 total per night from Nov 23 to Nov 24
$139 total
Nov 23 - Nov 24
Total with taxes and fees
Hotel Indigo Pittsburgh University-Oakland by IHG
329 Technology Drive Pittsburgh PA
Fully refundableReserve now, pay when you stay
$122 nightly
The price is $139 total per night from Nov 22 to Nov 23
$139 total
Nov 22 - Nov 23
Total with taxes and fees
8.6/10 Excellent! (1,003 reviews)
"The hotel front desk staff was amazing. Their free shuttle is pretty great, too! The restaurant, Eliza, was great and super allergy friendly. Although very understaffed which wasn’t their fault. But let’s talk about what was wrong. As soon as we entered our room we noticed it didn’t seem super clean. ..."
Reviewed on Nov 3, 2026
The Oaklander Hotel, Autograph Collection
5130 Bigelow Boulevard Pittsburgh PA
$199 nightly
The price is $227 total per night from Nov 23 to Nov 24
$227 total
Nov 23 - Nov 24
Total with taxes and fees
9.2/10 Wonderful! (853 reviews)
"Johnathan the bellhop went above and beyond to show us everything and gave helpful tips for the area"
Reviewed on Nov 2, 2026
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Stay near popular Oakland attractions
Things to do
Pittsburgh: Museum of Illusions Entrance Ticket
$29
per adult
86% of travellers recommend
Pittsburgh Bar Hunt: Party Through Pittsburgh Bar Crawl
$13
per adult
Pittsburgh: Pasta Making Class With Local Chef
$75
per adult
Explore a world of travel with Expedia
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- Visit Downtown Pittsburgh
- Schenley Park
- Carnegie Museum of Art
- Strip District Vacations
- Cathedral of Learning
- Pittsburgh Vacations
- Carnegie Mellon University
- North Shore Vacations
- National Aviary
- Acrisure Stadium
- Carnegie Library of Pittsburgh
- Byham Theater
- Carnegie Science Center
- Grandview Overlook
- Andy Warhol Bridge
- Children's Museum of Pittsburgh
- Monongahela Incline
- Senator John Heinz Regional History Centre
- Lighthouse ArtSpace Pittsburgh
- Visit Pittsburgh
- Duquesne Incline
- University of Pittsburgh
- Phipps Conservatory
- Ppg Paints Arena
- Kennywood
- Where to stay in Pittsburgh
- Roberto Clemente Bridge
- Andy Warhol Museum
- Petersen Events Center
- Point State Park
- The Nationality Rooms
- David L Lawrence Convention Center
- U.s. Steel Tower
- Heinz Memorial Chapel
- Soldiers and Sailors Memorial Hall and Museum
- Market Square
- Pnc Park
- Photo Antiquities Museum of Photographic History
- Carnegie Museum of Natural History
- Rachel Carson Bridge
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.